Glaucine

Short description: Chemical compound

Glaucine

Clinical data
AHFS/Drugs.com| International Drug Names
ATC code|

* none

Identifiers

IUPAC name

* (S)-5,6,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6-methyl-4H-dibenzo[de,g]quinoline

CAS Number|

* 475-81-0 Y
5630-11-5

PubChem CID|

* 16754

ChemSpider|

* 15883 N

UNII|

* NU19306XA7

KEGG|

* D08014 N

ChEBI|

* CHEBI:5373 N

ChEMBL|

* ChEMBL228082 N

NIAID ChemDB|

* 011385

Chemical and physical data
Formula| C21H25NO4
Molar mass| 355.434 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* CN1CCc2cc(c(c-3c2[C@@H]1Cc4c3cc(c(c4)OC)OC)OC)OC

InChI

* InChI=1S/C21H25NO4/c1-22-7-6-12-9-18(25-4)21(26-5)20-14-11-17(24-3)16(23-2)10-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3/t15-/m0/s1 N

* Key:RUZIUYOSRDWYQF-HNNXBMFYSA-N N

NY (what is this?) (verify)

Glaucine (1,2,9,10-TetraMethoxyAporphine, Bromcholitin, Glauvent, Tusidil, Tussiglaucin) is an aporphine alkaloid found in several different plant species in the family Papaveraceae such as Glaucium flavum,[1] Glaucium oxylobum and Corydalis yanhusuo,[2][3] and in other plants like Croton lechleri in the family Euphorbiaceae.[4]

It has bronchodilator, neuroleptic[5] and antiinflammatory effects, acting as a PDE4 inhibitor and calcium channel blocker,[6] and is used medically as an antitussive in some countries.[7] TLRs plays role in its anti inflammatory effects.[8] Glaucine may produce side effects such as sedation, fatigue, and a hallucinogenic effect characterised by colourful visual images,[9][10] and has been detected as a novel psychoactive drug.[11] In a 2019 publication,[12] the isomer (R)-glaucine is reported to be a positive allosteric modulator of the 5-HT2A receptor, which is also associated with the hallucinogenic effects of substances such as psilocybin and mescaline.

## Contents

* 1 Chemistry
* 1.1 Stereoisomerism
* 2 Mechanism of action
* 3 Uses
* 3.1 Medical
* 3.2 Recreational
* 4 See also
* 5 References

## Chemistry

### Stereoisomerism

It was believed that only the (S)-form of glaucine occurs in nature until (R)-glaucine was found in fire poppy (Papaver californicum).[13]

Glaucine
(2 stereoisomers)

(S)-configuration |
(R)-configuration

## Mechanism of action

Glaucine binds to the benzothiazepine site on L-type Ca2+-channels, thereby blocking calcium ion channels in smooth muscle like the human bronchus. Glaucine has no effect on intracellular calcium stores, but rather, does not allow the entry of Ca2+ after intracellular stores have been depleted.[6] Ca2+ influx is a vital component in the process of muscular contraction, and the blocking of this influx therefore reduces the ability of the muscle to contract.[14] In this way, glaucine can prevent smooth muscle from contracting, allowing it to relax.

Glaucine has also been demonstrated to be a dopamine receptor antagonist, favoring D1 and D1-like receptors.[11][15] It is also a non-competitive selective inhibitor of PDE4 in human bronchial tissue and granulocytes. PDE4 is an isoenzyme that hydrolyzes cyclic AMP to regulate human bronchial tone (along with PDE3). Yet as a PDE4 inhibitor, glaucine possesses very low potency.[6]

Glaucine has also recently[12] been found to have an effect on the neuronal 5-HT2A receptors, which are responsible for the hallucinogenic effects of classical psychedelics. It also inhibits MAO enzymes.[16] Its enantiomers effect are same for adrenergic receptor yet different for 5-HT receptor. Both (R)-Glaucine and (S)-Glaucine antagonizes α1 receptor but (S)-Glaucine is partial agonist of 5-HT2 subtypes whereas (R)-Glaucine is positive allosteric modulator of 5-HT2.[17]

## Uses

### Medical

It is currently used as an antitussive agent in Iceland, as well as Romania, Bulgaria, Russia and other eastern European countries.[6][11] Bulgarian pharmaceutical company Sopharma sells glaucine in tablet form, where a single dose contains 40 mg and the half-life is indicated to be 6–8 hours. When ingested orally has been shown to increase airway conductance in humans, and has been investigated as a treatment for asthma.[6]

Glaucine has been reported to reduce blood pressure, heart rate and possess anticonvulsant and antinoiciceptive effect in animals[18][19]

### Recreational

Reports of recreational use of glaucine have recently been published, and effects include dissociative-type symptoms; feeling detached and 'in another world', as well as nausea, vomiting and dilated pupils. These reports mirror those about the effects of clinical use, which state dissociative-type symptoms as well as lethargy, fatigue, hallucinations.[10][11] Investigation of side effects in a clinical setting also reports that the hallucinatory effects manifest as bright and colorful visualizations. They also report that patients perceive their environments clearly yet feel detached from it; "the patient sees and understands everything and is oriented well enough, but cannot take a clear and adequate action".[10]

One particular report of recreational use gone awry described the form of distribution as tablets being marketed as a 1-benzylpiperazine (BZP)-free "herbal high" which the patient referred to as "head candy".[11]

## See also

## References

1. ↑ "HPLC Determination of Glaucine in Yellow Horn Poppy Grass (Glaucium flavum Crantz)". Pharmaceutical Chemistry Journal 38 (1): 441–442. August 2004. doi:10.1023/B:PHAC.0000048907.58847.c6. ISSN 0091-150X. "S-(+)-Glaucine (C21H25NO4) is the main alkaloid component in the grass of yellow horn poppy (Glaucium luteum L., syn. Glaucium flavum Crantz) of the family Papaveraceae".
2. ↑ "[Resource investigation and quality evaluation on wild Corydalis yanhusuo]". Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica 29 (5): 399–401. May 2004. PMID 15706885.
3. ↑ "Antifungal activity of the methanolic extract and alkaloids of Glaucium oxylobum". Fitoterapia 74 (5): 493–6. July 2003. doi:10.1016/s0367-326x(03)00113-8. PMID 12837370.
4. ↑ "Geographic distribution of three alkaloid chemotypes of Croton lechleri". Journal of Natural Products 65 (6): 814–9. June 2002. doi:10.1021/np000270v. PMID 12088421.
5. ↑ "Neuroleptic-like, anticonvulsant and antinociceptive effects of aporphine alkaloids: bulbocapnine, corytuberine, boldine and glaucine". Archives Internationales de Pharmacodynamie et de Therapie 296: 255–281. 1988. PMID 2907279.
6. ↑ 6.0 6.1 6.2 6.3 6.4 "Bronchodilator and anti-inflammatory activities of glaucine: In vitro studies in human airway smooth muscle and polymorphonuclear leukocytes". British Journal of Pharmacology 127 (7): 1641–51. August 1999. doi:10.1038/sj.bjp.0702702. PMID 10455321.
7. ↑ "Objective evaluation of dextromethorphan and glaucine as antitussive agents". British Journal of Clinical Pharmacology 17 (5): 521–4. May 1984. doi:10.1111/j.1365-2125.1984.tb02384.x. PMID 6375709.
8. ↑ "Toll-like receptor-mediated anti-inflammatory action of glaucine and oxoglaucine". Fitoterapia 80 (7): 411–4. October 2009. doi:10.1016/j.fitote.2009.05.016. PMID 19481591. https://hal-riip.archives-ouvertes.fr/pasteur-00736334/file/Fitoterapia_Ivanovska.pdf.
9. ↑ "[A case of hallucinogen-like action of glaucine]". Klinicheskaia Meditsina 67 (9): 107–8. September 1989. PMID 2586025.
10. ↑ 10.0 10.1 10.2 "[Acute glaucine syndrome in the physician's practice: the clinical picture and potential danger]". Klinicheskaia Meditsina 84 (11): 68–70. 2006. PMID 17243616.
11. ↑ 11.0 11.1 11.2 11.3 11.4 "Detection of the pharmaceutical agent glaucine as a recreational drug". European Journal of Clinical Pharmacology 64 (5): 553–4. May 2008. doi:10.1007/s00228-007-0451-9. PMID 18204834.
12. ↑ 12.0 12.1 Heng, HL, Chee, CF, Thy, CK, et al. In vitro functional evaluation of isolaureline, dicentrine and glaucine enantiomers at 5‐HT2 and α1 receptors. Chem Biol Drug Des. 2019; 93: 132– 138. https://doi.org/10.1111/cbdd.13390
13. ↑ "A functionally conserved STORR gene fusion in Papaver species that diverged 16.8 million years ago". Nature Communications 13 (1): 3150. June 2022. doi:10.1038/s41467-022-30856-w. PMID 35672295. Bibcode: 2022NatCo..13.3150C.
14. ↑ Nestler E, Hyman S & Malenka R. Molecular Neuropharmacology: A Foundation for Clinical Neuroscience (2nd ed.). China: McGraw-Hill Companies.
15. ↑ "Structure-affinity relationships of halogenated predicentrine and glaucine derivatives at D1 and D2 dopaminergic receptors: halogenation and D1 receptor selectivity". Bioorganic & Medicinal Chemistry 13 (11): 3699–704. June 2005. doi:10.1016/j.bmc.2005.03.022. PMID 15862999.
16. ↑ "Rapid screening and identification of monoamine oxidase-A inhibitors from Corydalis Rhizome using enzyme-immobilized magnetic beads based method". Journal of Chromatography A 1592: 1–8. May 2019. doi:10.1016/j.chroma.2019.01.062. PMID 30712820.
17. ↑ "In vitro functional evaluation of isolaureline, dicentrine and glaucine enantiomers at 5-HT2 and α1 receptors". Chemical Biology & Drug Design 93 (2): 132–138. February 2019. doi:10.1111/cbdd.13390. PMID 30216681.
18. ↑ "Neuroleptic-like, anticonvulsant and antinociceptive effects of aporphine alkaloids: bulbocapnine, corytuberine, boldine and glaucine". Archives Internationales de Pharmacodynamie et de Therapie 296: 255–81. 1988. PMID 2907279.
19. ↑ "Study of the in vivo and in vitro cardiovascular effects of (+)-glaucine and N-carbethoxysecoglaucine in rats". British Journal of Pharmacology 114 (7): 1419–27. April 1995. doi:10.1111/j.1476-5381.1995.tb13364.x. PMID 7606346.

* v
* t
* e

Cough and cold preparations (R05)

Expectorants|

* Althea root
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Mucolytics|

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Cough suppressants|

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opioids,
and derivatives|

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|

Other|

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* #WHO-EM
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* t
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Hallucinogens

Psychedelics
(5-HT2A
agonists)|

| Benzofurans|

* 2C-B-FLY
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|

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Phenethyl‐
amines|

| 2C-x|

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* 2C-Bu
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| 25x-NBx|

| 25x-NB3OMe|

* 25B-NB3OMe
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* 25E-NB3OMe
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* 25I-NB3OMe
* 25N-NB3OMe
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* 25T2-NB3OMe
* 25T4-NB3OMe
* 25T7-NB3OMe
* 25TFM-NB3OMe

|

25x-NB4OMe|

* 25B-NB4OMe
* 25C-NB4OMe
* 25D-NB4OMe
* 25E-NB4OMe
* 25H-NB4OMe
* 25I-NB4OMe
* 25N-NB4OMe
* 25P-NB4OMe
* 25T2-NB4OMe
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* 25T7-NB4OMe
* 25TFM-NB4OMe

25x-NBF|

* 25B-NBF
* 25C-NBF
* 25D-NBF
* 25E-NBF
* 25H-NBF
* 25I-NBF
* 25P-NBF
* 25T2-NBF
* 25T7-NBF
* 25TFM-NBF

25x-NBMD|

* 25B-NBMD
* 25C-NBMD
* 25D-NBMD
* 25E-NBMD
* 25F-NBMD
* 25H-NBMD
* 25I-NBMD
* 25P-NBMD
* 25T2-NBMD
* 25T7-NBMD
* 25TFM-NBMD

25x-NBOH|

* 25B-NBOH
* 25C-NBOH
* 25CN-NBOH
* 25D-NBOH
* 25E-NBOH
* 25F-NBOH
* 25H-NBOH
* 25I-NBOH
* 25P-NBOH
* 25T2-NBOH
* 25T7-NBOH
* 25TFM-NBOH

25x-NBOMe|

* 25B-NBOMe
* 25C-NBOMe
* 25CN-NBOMe
* 25D-NBOMe
* 25E-NBOMe
* 25F-NBOMe
* 25G-NBOMe
* 25H-NBOMe
* 25I-NBOMe
* 25iP-NBOMe
* 25N-NBOMe
* 25P-NBOMe
* 25T2-NBOMe
* 25T4-NBOMe
* 25T7-NBOMe
* 25TFM-NBOMe

Atypical structures|

* 25I-NB34MD
* 2CBCB-NBOMe
* 2CBFly-NBOMe
* NBOMe-mescaline

3C-x|

* 3C-AL
* 3C-BZ
* 3C-DFE
* 3C-E
* 3C-P

4C-x|

* 4C-B
* 4C-D
* 4C-T-2

DOx|

* DOT
* DOB
* DOC
* DOEF
* DOET
* DOF
* DOI
* DOiPR
* DOM
* DON
* DOPR
* DOTFM
* MEM

HOT-x|

* HOT-2
* HOT-7
* HOT-17

MDxx|

* DMMDA
* DMMDA-2
* Lophophine
* MDA
* MMDA
* MMDA-2
* MMDA-3a
* MMDMA

Mescaline (subst.)|

* 2-Bromomescaline
* 3-TE
* 4-TE
* 3-TM
* 4-TM
* Allylescaline
* Asymbescaline
* Buscaline
* Cyclopropylmescaline
* Difluoromescaline
* Difluoroescaline
* Escaline
* Fluoroproscaline
* Isobuscaline
* Isoproscaline
* Jimscaline
* Mescaline
* Metaescaline
* Methallylescaline
* Proscaline
* Thioproscaline
* Trifluoroescaline
* Trifluoromescaline

TMAs|

* TMA
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* TMA-4
* TMA-5
* TMA-6

Others|

* 2C-B-BUTTERFLY
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* DESOXY
* DMCPA
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* Fenfluramine
* Ganesha
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* MMA
* TCB-2
* TOMSO

Piperazines|

* BZP
* pFPP

Tryptamines|

| alpha-alkyltryptamines|

* 4,5-DHP-α-MT
* 5-MeO-α-ET
* 5-MeO-α-MT
* α-ET
* α-MT

|

x-DALT|

* (Daltocin) 4-HO-DALT
* (Daltacetin) 4-AcO-DALT
* 5-MeO-DALT
* DALT

x-DET|

* (Ethacetin) 4-AcO-DET
* (Ethocin) 4-HO-DET
* 5-MeO-DET
* (T-9) DET
* (Ethocybin) 4-PO-DET

x-DiPT|

* (Ipracetin) 4-AcO-DiPT
* (Iprocin) 4-HO-DiPT
* 5-MeO-DiPT
* DiPT

x-DMT|

* 4,5-DHP-DMT
* 2,N,N-TMT
* 4-AcO-DMT
* 4-HO-5-MeO-DMT
* 4,N,N-TMT
* 4-Propionyloxy-DMT
* 5,6-diBr-DMT
* 5-AcO-DMT
* 5-Bromo-DMT
* 5-MeO-2,N,N-TMT
* 5-MeO-4,N,N-TMT
* 5-MeO-α,N,N-TMT
* 5-MeO-DMT
* 5-N,N-TMT
* 7,N,N-TMT
* α,N,N-TMT
* (Bufotenin) 5-HO-DMT
* DMT
* Norbaeocystin
* (Psilocin) 4-HO-DMT
* (Psilocybin) 4-PO-DMT

x-DPT|

* (Depracetin) 4-AcO-DPT
* (Deprocin) 4-HO-DPT
* 5-MeO-DPT
* (The Light) DPT

Ibogaine-related|

* 18-MAC
* 18-MC
* Coronaridine
* Ibogaine
* Ibogamine
* ME-18-MC
* Noribogaine
* Tabernanthine
* Voacangine

x-MET|

* (Metocin) 4-HO-MET
* (Metocetin) 4-AcO-MET
* 5-MeO-MET
* MET

x-MiPT|

* (Mipracetin) 4-AcO-MiPT
* (Miprocin) 4-HO-MiPT
* 5-Me-MiPT
* (Moxy) 5-MeO-MiPT
* MiPT

Others|

* 4-HO-DBT
* 4-HO-EPT
* 4-HO-McPT
* (Lucigenol) 4-HO-MPMI
* (Meprocin) 4-HO-MPT
* 5-MeO-EiPT
* 5-MeO-MALT
* 5-MeO-MPMI
* Aeruginascin
* Baeocystin
* DBT
* DCPT
* EiPT
* EPT
* MPT
* PiPT

Others|

* AL-38022A
* ALPHA
* Dimemebfe
* Efavirenz
* Lorcaserin
* M-ALPHA
* RH-34
Also empathogens in general (e. g.: 5-APB, 5-MAPB]], 6-APB and other substituted benzofurans, Chemistry:MDAI

Dissociatives
(NMDAR
antagonists)|

| Arylcyclo‐
hexylamines|

| Ketamine-related|

* 2-Fluorodeschloroketamine
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* Deschloroketamine
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* Esketamine ((S)-ketamine)
* Ketamine
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* Methoxmetamine
* Methoxyketamine
* Norketamine
* Tiletamine

|

PCP-related|

* 3'-HO-PCP
* 3'-MeO-PCE
* 3'-MeO-PCMo
* 3'-MeO-PCP
* BDPC
* Dieticyclidine (PCDE)
* Eticyclidine (PCE)
* Methoxydine (4'-MeO-PCP)
* PCPr
* Phencyclidine (PCP)
* Rolicyclidine (PCPy)
* Tenocyclidine (TCP)

Others|

* BTCP
* Gacyclidine
* PRE-084

Diarylethylamines|

* Diphenidine
* Ephenidine
* Fluorolintane
* Methoxphenidine

Morphinans|

* Dextrallorphan
* Dextromethorphan
* Dextrorphan
* Racemethorphan
* Racemorphan

Others|

* 2-EMSB
* 2-MDP
* 8A-PDHQ
* Aptiganel
* Budipine
* Delucemine
* Dexoxadrol
* Dizocilpine
* Etoxadrol
* Herkinorin
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* Nitrous oxide
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Deliriants
(mAChR
antagonists)|

* Atropine
* Benactyzine
* Benzatropine
* Benzydamine
* Biperiden
* BRN-1484501
* Brompheniramine
* BZ
* CAR-226,086
* CAR-301,060
* CAR-302,196
* CAR-302,282
* CAR-302,368
* CAR-302,537
* CAR-302,668
* Chloropyramine
* Chlorphenamine
* Clemastine
* CS-27349
* Cyclizine
* Cyproheptadine
* Dicycloverine
* Dimenhydrinate
* Diphenhydramine
* Ditran
* Doxylamine
* EA-3167
* EA-3443
* EA-3580
* EA-3834
* Elemicin
* Flavoxate
* Hyoscyamine
* JB-318
* JB-336
* Meclozine
* Mepyramine
* Myristicin
* Orphenadrine
* Oxybutynin
* Pheniramine
* Phenyltoloxamine
* Procyclidine
* Promethazine
* Scopolamine
* Tolterodine
* Trihexyphenidyl
* Tripelennamine
* Triprolidine
* WIN-2299

Others|

| Cannabinoids
(CB1 agonists)|

| Natural|

* THC (Dronabinol)
* THCV

|

Synthetic|

| AM-x|

* AM-087
* AM-251
* AM-279
* AM-281
* AM-356
* AM-374
* AM-381
* AM-404
* AM-411
* AM-630
* AM-661
* AM-678
* AM-679
* AM-694
* AM-735
* AM-855
* AM-881
* AM-883
* AM-905
* AM-906
* AM-919
* AM-926
* AM-938
* AM-1116
* AM-1172
* AM-1220
* AM-1221
* AM-1235
* AM-1241
* AM-1248
* AM-1710
* AM-1714
* AM-1902
* AM-2201
* AM-2212
* AM-2213
* AM-2232
* AM-2233
* AM-2389
* AM-3102
* AM-4030
* AM-4054
* AM-4056
* AM-4113
* AM-6545

|

CP x|

* CP 47,497
* CP 55,244
* CP 55,940
* (±)-CP 55,940
* (+)-CP 55,940
* (-)-CP 55,940

HU-x|

* HU-210
* HU-211
* HU-239
* HU-243
* HU-308
* HU-320
* HU-331
* HU-336
* HU-345

JWH-x|

* JWH-007
* JWH-015
* JWH-018
* JWH-019
* JWH-030
* JWH-047
* JWH-048
* JWH-051
* JWH-057
* JWH-073
* JWH-081
* JWH-098
* JWH-116
* JWH-120
* JWH-122
* JWH-133
* JWH-139
* JWH-147
* JWH-148
* JWH-149
* JWH-149
* JWH-161
* JWH-164
* JWH-166
* JWH-167
* JWH-171
* JWH-175
* JWH-176
* JWH-181
* JWH-182
* JWH-184
* JWH-185
* JWH-192
* JWH-193
* JWH-193
* JWH-194
* JWH-195
* JWH-196
* JWH-197
* JWH-198
* JWH-199
* JWH-200
* JWH-203
* JWH-205
* JWH-210
* JWH-210
* JWH-213
* JWH-220
* JWH-229
* JWH-234
* JWH-249
* JWH-250
* JWH-251
* JWH-253
* JWH-258
* JWH-300
* JWH-302
* JWH-307
* JWH-336
* JWH-350
* JWH-359
* JWH-387
* JWH-398
* JWH-424

Misc. designer cannabinoids|

* 4-HTMPIPO
* 5F-AB-FUPPYCA
* 5F-AB-PINACA
* 5F-ADB
* 5F-ADB-PINACA
* 5F-ADBICA
* 5F-AMB
* 5F-APINACA
* 5F-CUMYL-PINACA
* 5F-NNE1
* 5F-PB-22
* 5F-SDB-006
* A-796,260
* A-836,339
* AB-001
* AB-005
* AB-CHFUPYCA
* AB-CHMINACA
* AB-FUBINACA
* AB-PINACA
* ADAMANTYL-THPINACA
* ADB-CHMINACA
* ADB-FUBINACA
* ADB-PINACA
* ADBICA
* ADSB-FUB-187
* AMB-FUBINACA
* APICA
* APINACA
* APP-FUBINACA
* CB-13
* CUMYL-PICA
* CUMYL-PINACA
* CUMYL-THPINACA
* DMHP
* EAM-2201
* FAB-144
* FDU-PB-22
* FUB-144
* FUB-APINACA
* FUB-JWH-018
* FUB-PB-22
* FUBIMINA
* JTE 7-31
* JTE-907
* Levonantradol
* MDMB-CHMICA
* MDMB-CHMINACA
* MDMB-FUBINACA
* MEPIRAPIM
* MAM-2201
* MDA-19
* MN-18
* MN-25
* NESS-0327
* NESS-040C5
* Nabilone
* Nabitan
* NM-2201
* NNE1
* Org 28611
* Parahexyl
* PTI-1
* PTI-2
* PX-1
* PX-2
* PX-3
* QUCHIC
* QUPIC
* RCS-4
* RCS-8
* SDB-005
* SDB-006
* STS-135
* THC-O-acetate
* THC-O-phosphate
* THJ-018
* THJ-2201
* UR-144
* WIN 55,212-2
* XLR-11

D2 agonists|

* Apomorphine
* Aporphine
* Bromocriptine
* Cabergoline
* Lisuride
* Memantine
* Nuciferine
* Pergolide
* Phenethylamine
* Piribedil
* Pramipexole
* Ropinirole
* Rotigotine
* Salvinorin A
Also indirect D2 agonists, such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa).

GABAA
enhancers|

* CI-966
* Eszopiclone
* Ibotenic acid
* Muscimol (Amanita muscaria)
* Zaleplon
* Zolpidem
* Zopiclone

Inhalants
(Mixed MOA)|

* Aliphatic hydrocarbons
* Butane
* Gasoline
* Kerosene
* Propane
* Aromatic hydrocarbons
* Toluene
* Ethers
* Diethyl ether
* Enflurane
* Haloalkanes
* Chlorofluorocarbons
* Chloroform

κOR agonists|

* 2-EMSB
* Alazocine
* Bremazocine
* Butorphan
* Butorphanol
* Cyclazocine
* Cyclorphan
* Cyprenorphine
* Diprenorphine
* Enadoline
* Herkinorin
* Heroin
* HZ-2
* Ibogaine
* Ketazocine
* Levallorphan
* Levomethorphan
* Levorphanol
* LPK-26
* Metazocine
* Morphine
* Nalbuphine
* Nalmefene
* Nalorphine
* Noribogaine
* Oxilorphan
* Pentazocine
* Phenazocine
* Proxorphan
* Racemethorphan
* Racemorphan
* Salvinorin A
* Spiradoline
* Tifluadom
* U-50488
* U-69,593
* Xorphanol

Others|

* Glaucine
* Isoaminile
* Noscapine
* Pukateine

* v
* t
* e

Phosphodiesterase inhibitors

PDE1|

* MMPX
* SCH-51866
* Vinpocetine

PDE2|

* BAY 60-7550
* Carbazeran
* EHNA
* Oxindole
* PDP

PDE3|

* Adibendan
* Amrinone (inamrinone)
* Anagrelide
* Benafentrine
* Bucladesine
* Carbazeran
* Cilostamide
* Cilostazol
* Enoximone
* Imazodan
* KMUP-1
* Meribendan
* Milrinone
* Olprinone
* Parogrelil
* Pimobendan
* Pumafentrine
* Quazinone
* RPL-554
* Siguazodan
* Trequinsin
* Vesnarinone
* Zardaverine

PDE4|

* Apremilast
* Arofylline
* Atizoram
* Benafentrine
* Catramilast
* CC-1088
* CDP-840
* CGH-2466
* Cilomilast
* Cipamfylline
* Crisaborole
* Denbutylline
* Difamilast
* Drotaverine
* Etazolate
* Filaminast
* Glaucine
* HT-0712
* ICI-63197
* Indimilast
* Irsogladine
* Lavamilast
* Lirimilast
* Lotamilast
* Luteolin
* Mesembrenone
* Mesembrine
* Mesopram
* Oglemilast
* Piclamilast
* Pumafentrine
* Revamilast
* Ro 20-1724
* Roflumilast
* Rolipram
* Ronomilast
* RPL-554
* RS-25344
* Tetomilast
* Tofimilast
* YM-976
* Zardaverine

PDE5|

* Acetildenafil
* Aildenafil
* Avanafil
* Beminafil
* Benzamidenafil
* Dasantafil
* Icariin
* Gisadenafil
* Homosildenafil
* Lodenafil
* Mirodenafil
* MY-5445
* Nitrosoprodenafil
* Norcarbodenafil
* SCH-51866
* Sildenafil
* Sulfoaildenafil
* T-0156
* Tadalafil
* Udenafil
* Vardenafil

PDE7|

* BRL-50481

PDE9|

* BAY 73-6691
* PF-04447943
* Paraxanthine

PDE10|

* Balipodect
* Mardepodect
* Papaverine
* TC-E 5005
* Tofisopam

PDE11|

BC11-38

Non-selective|

* Aminophylline
* Caffeine
* Choline theophyllinate
* CPX
* Dipyridamole
* Doxofylline
* Enprofylline
* Ibudilast
* IBMX
* Luteolin
* Pentoxifylline
* Propentofylline
* Theobromine
* Theophylline
* Zaprinast

Unsorted|

* Diazepam
* Diprophylline
* DPCPX
* Furafylline
* Lisofylline
* MDL-12330A
* Moxaverine
* Oxagrelate
* Pentifylline
* Proxyphylline
* Quercetin
* Satigrel
* Tolafentrine
* Trapidil

See also: Receptor/signaling modulators

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Original source: https://en.wikipedia.org/wiki/Glaucine. Read more

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Glaucine&oldid=3331533"
*[CID]: Compound ID
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[NB3OMe]: NB: N-benzyl; 3OMe: 3-methoxy
*[NB4OMe]: NB: N-benzyl; 4OMe: 4-methoxy
*[NBF]: NB: N-benzyl; F: fluoro
*[NBMD]: NB: N-benzyl; MD: methylenedioxy
*[NBOH]: NB: N-benzyl; OH: hydroxy
*[NBOMe]: NB: N-benzyl; OMe: methoxy
*[DALT]: N,N-Diallyltryptamine
*[DET]: N,N-Diethyltryptamine
*[DiPT]: N,N-Diisopropyltryptamine
*[DMT]: N,N-Dimethyltryptamine
*[DPT]: N,N-Dipropyltryptamine
*[MET]: N-Methyl-N-ethyltryptamine
*[MiPT]: N-Methyl-N-isopropyltryptamine